Biocatalytic Parallel Interconnected Dynamic Asymmetric Disproportionation of α-Substituted Aldehydes: Atom-Efficient Access to Enantiopure (S )-Profens and Profenols

Advanced Synthesis & Catalysis
Erika TassanoMélanie Hall

Abstract

The biocatalytic asymmetric disproportionation of aldehydes catalyzed by horse liver alcohol dehydrogenase (HLADH) was assessed in detail on a series of racemic 2-arylpropanals. Statistical optimization by means of design of experiments (DoE) allowed the identification of critical interdependencies between several reaction parameters and revealed a specific experimental window for reaching an 'optimal compromise' in the reaction outcome. The biocatalytic system could be applied to a variety of 2-arylpropanals and granted access in a redox-neutral manner to enantioenriched (S)-profens and profenols following a parallel interconnected dynamic asymmetric transformation (PIDAT). The reaction can be performed in aqueous buffer at ambient conditions, does not rely on a sacrificial co-substrate, and requires only catalytic amounts of cofactor and a single enzyme. The high atom-efficiency was exemplified by the conversion of 75 mM of rac-2-phenylpropanal with 0.03 mol% of HLADH in the presence of ∼0.013 eq. of oxidized nicotinamide adenine dinucleotide (NAD+), yielding 28.1 mM of (S)-2-phenylpropanol in 96% ee and 26.5 mM of (S)-2-phenylpropionic acid in 89% ee, in 73% overall conversion. Isolated yield of 62% was obtained on 100 mg-sc...Continue Reading

References

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Aug 18, 2017·Journal of the American Chemical Society·Morgane GaydouRuben Martin

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Citations

Nov 2, 2019·Chemical Society Reviews·Erika Tassano, Mélanie Hall
May 12, 2020·Chemical Communications : Chem Comm·Erika TassanoMélanie Hall
Apr 25, 2020·Angewandte Chemie·Frank HollmannCaroline E Paul
Jun 21, 2021·Biotechnology Advances·David RibeaucourtJean-Guy Berrin
Aug 31, 2021·RSC Chemical Biology·Mélanie Hall
Oct 13, 2021·BMC Biotechnology·Christian RappRegina Kratzer

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Methods Mentioned

BETA
HLADH

Software Mentioned

Stat
PIDAT
Design
DesignExpert®

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